Crystal structure of (3 E)-5-nitro-3-(2-phenyl-hydrazinyl-idene)-1 H-indol-2(3 H)-one

Jecika Maciel Velasques; Vanessa Carratu Gervini; Adaílton João Bortoluzzi; Renan Lira de Farias; Adriano Bof de Oliveira

doi:10.1107/S2056989016020375

Crystal structure of (3 E)-5-nitro-3-(2-phenyl-hydrazinyl-idene)-1 H-indol-2(3 H)-one

Acta Crystallogr E Crystallogr Commun. 2017 Jan 13;73(Pt 2):168-172. doi: 10.1107/S2056989016020375. eCollection 2017 Feb 1.

Authors

Jecika Maciel Velasques¹, Vanessa Carratu Gervini¹, Adaílton João Bortoluzzi², Renan Lira de Farias³, Adriano Bof de Oliveira⁴

Affiliations

¹ Universidade Federal do Rio Grande (FURG), Escola de Química e Alimentos, Rio Grande, Brazil.
² Universidade Federal de Santa Catarina (UFSC), Departamento de Química, Florianópolis, Brazil.
³ Universidade Estadual Paulista (UNESP), Instituto de Química, Araraquara, Brazil.
⁴ Universidade Federal de Sergipe (UFS), Departamento de Química, São Cristóvão, Brazil.

Abstract

The reaction between 5-nitro-isatin and phenyl-hydrazine in acidic ethanol yields the title compound, C₁₄H₁₀N₄O₃, whose mol-ecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065 Å for the mean plane through all non-H atoms). An intra-molecular N-H⋯O hydrogen bond is present, forming a ring of graph-set motif S(6). In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen-bonding inter-actions into a two-dimensional network along (120), and rings of graph-set motif R₂²(8), R₂²(26) and R₄⁴(32) are observed. Additionally, a Hirshfeld surface analysis suggests that the mol-ecules are stacked along [100] through C=O⋯Cg inter-actions and indicates that the most important contributions for the crystal structure are O⋯H (28.5%) and H⋯H (26.7%) inter-actions. An in silico evaluation of the title compound with the DHFR enzyme (di-hydro-folate reductase) was performed. The isatin-hydrazone derivative and the active site of the selected enzyme show N-H⋯O(ASP29), N-H⋯O(ILE96) and Cg⋯Cg(PHE33) inter-actions.

Keywords: Hirshfeld surface calculation; crystal structure; in silico evaluation; isatin–hydrazone derivative; two-dimensional hydrogen-bonded network.